Many a Winding Turn
by PrincessCheese
Summary: Based on an idea from the books. AU after "The EX files". OC/Blair/Chuck triangle with a twist.
1. Chapter 1

****** I own nothing all the characters belong to other people that aren't me******

**AU –This is set 6 months after the ex-files. Everything after that episode never happened. Serena is Queen S but Blair is Prime Minister (a concept I read in a fic and love the idea of a Queen is just a figure head and B could be so much more). Both girls have spent the last 6 months being socialistas and partying almost constantly. **

**This fic does have a OOC for Blair's love interest so I understand if C/B shippers find it difficult however I am nothing if I am not C/B til the end and despite being a little in love with my OOC Waldass are inevitable. **

**I have this fic planned out but it's not my usual style so a beta or even just someone to bounce some ideas off and help with plot development would be awesomeness. **

* * *

Blair looked around the pub, the dark wood and burgundy seating made it look more intimate and cosy than the sleek and minimalist bars that she usually went to. She rolled her eyes at the place, she hated themed bars and of all themed bars she could imagine _O'Reilly's_ "Traditional Irish Pub" in the middle of New York had to be the worst.

"Remind me S, what are you doing here? Why not 151, L'Oak or even god forbid the lair of the devil himself" she asked her best friend who was more than slightly distracted making eyes at a tall tanned guy with dark brown hair and rippling muscles, he kind of looked like someone had put Dan's face on Nates body then aged him 5 years, Serena was hooked.

"You would never go to Victrola, it would go against your genius plan of avoiding Chuck until graduation!" Serena slurred in response, her slightly glazed eyes never leaving the object of her affection. "Anyway I just watched P.S. I love you again and I have decided that I want my very own Gerard Butler"

"I am not avoiding Chuck, we are friends and Gerard Butler is Scottish!" Blair moaned, more to herself than Serena because Serena was already making her way over to the man she hadn't been able to take her eyes off. "I bet this place doesn't even do Apple Martini's"

"No, but I could drop a dash of Blackcurrant into your Guinness if you like" a thick Irish accent responded from behind the bar.

"As lovely as that sounds, I don't drink… stout." She shot him her fakest smile and turned back to see Serena flirting shamelessly with the guy. It was going to be a long night; she may as well keep herself entertained. "So do they pay you extra to put that accent on? Is it supposed to drive the "punters" crazy?"

"They barely pay me at all and the accents real." He smiled at her and for a moment the Blair Waldorf calm threatened to abandon her. "Come on your can't come to _O'Reilly's_ without having a Guinness, it's a tradition. Unless you are too scared that is, I mean it's a big drink for a wee lass like you."

Blair rolled her eyes; did this guy think he was dealing with a freshman? His completely obvious attempts at manipulation strangely endeared her to him, meeting someone so clueless was a rarity in her world. Even Jenny Humphrey a freshman from Brooklyn had more wile and was willing to hit lower blows than even she expected. She decided to have fun with this guy since by this point Serena was playing tonsil hockey with the dark haired Casanova. She held out her hand "Blair, and you are?"

"Donald, but my friends call me Donny" his blue eyes sparkled as he stared intensely at her, his smirk going all the way up to his eyes.

"Well Donny, how about we make things interesting, pour two pints of Guinness, if I finish mine before you do you make me an apple martini and keep them coming."

"And if I beat you?" he countered

"I'll leave you in peace?" she offered

"I get a date"

Blair looked at him, a crooked smile played on her lips, she didn't know if it was the fact that Serena her so called sister in singledom was currently engaged in a passionate liplock, or the fact that she hadn't had a glimpse of old fashioned romance since she had found out that "the Lord" was as kinky as he was boring, maybe it was just because Donny was gorgeous, his accent made her feel weak at the knees and the tinkle in his eyes just made her want to smile but she found herself agreeing.

As they waiting for their drinks, Guinness took an infamously long time to pour, she discovered that Donny O'Reilly's mother was from Brooklyn but moved to Ireland to live with her grandparents when she fell pregnant, he was born and raised in Galway West Ireland and moved to America when he graduated college to help his grandfather run his bar, pursue his career and get to know the family his mother left behind.

"So Miss Blair, tell me about you"

"My Dad lives in France, my mom designs clothes for a living, I'm going to Yale in the fall and I've lived in New York all my life, which kind of explains why I'm here. Serena, my best friend, wants us to do the tourist thing before we leave so I watched the St Patrick's Day parade and now I am here."

"Drinks are ready, start drinking after 3" he passed her the pint glass; it was full of dark thick liquid with even thicker foam on top of it. She gulped as she assessed the challenge, unsure if it was the heart that he had drawn in the foam with the nozzle of the pump or the fact that she was about to attempt to down a drink the consistency of soup that made her stomach do a somersault.

" 1,2,3" she shouted quickly before knocking back the glass, the thick malty liquid tasted disgusting and at one moment she thought she might throw it all up but as she relaxed her throat it seemed to get easier to let it slide down. As she swallowed the final drops she slammed the glass down on the counter and for the first time dared to look at Donny, who was looking at her with an empty glass and a massive smile on his face.

"So Blair, how does Friday at 8 sound?" she didn't think it was possible but his smile actually got wider.

Blair hated to lose, and despite the fact that seeing him again was not exactly the worse prospect in the world, she was still Blair Waldorf and he was a barman from Brooklyn, she wasn't queen anymore and if she started dating brooklynites it would only be a matter of time before someone decided to call an election. She had spent enough time with Chuck to know what the best thing to do in the face of defeat is to change the rules. "Sounds like a date, but only if you help me get my very drunk friend away from Fabio over there." She nodded towards the corner of the bar in which Serena was still getting down and dirty with the tanned Adonis from earlier.

"The gorgeous Blonde?" Donny asked, his eyes resting on Serena for just long enough for Blair to feel both the Guinness she had just drunk and the boiled bacon and cabbage that Serena had forced her sample despite her trepidation beginning to resurface. .

"Yeah that's Serena" Blair snapped, it hurt a little to think that anyone who seemed interested in her could so easily be distracted by her beautiful best friend.

"Well Fabio as you put it, is actually my friend Jonas, she is perfectly safe, he is a grand fella, wouldn't harm a hair on her little blonde head." He looked at her quizzically, studying her face wondering where the bitterness in her voice had come from.

"Not as reassuring as it could be whilst his tongue is down her throat. Don't worry I can do it myself wouldn't be the first time." She marched over to Serena, barely excusing herself and grabbed her arm yanking her out of Jonas' arms.

"Blair what the hell, we were in the middle of something" Serena shouted at her friend.

"Serena, you are drunk and I am tired we are going!" Blair hissed trying again to pull her friend towards the exit.

"No I'm staying here with Jonas, we are having fun. You are such a spoil sport Blair Waldorf; you don't want me to have fun because you can't have any." Serena pulled her arm back and giggled, she squared up to the brunette taking full advantage of the height difference "Don't blame me for having fun just because you are still hung up on Chuckles."

Blair face was full of fury, a drunken Serena was known for her low blows but bringing up Chuck was taking things too far, Blair had to get her friend out of there whilst they still had a friendship.

In the 6 months since school had restarted Serena had been steadily reverting back to how she was before boarding school, the decline had increased since Christmas when Lily had announced that she was leaving Bart for Rufus and the boy who had broken her heart had overnight become her brother.

At first Blair enjoyed the fun and escape of being on an almost constant booze fuelled rampage it certainly lead to fewer questions about why she couldn't keep her breakfast down… or her lunch. But she was getting tired, tired of the nights and strangers and increasingly worried what trouble Serena's constant need for attention would get her into.

"Serena Van Der Woodsen, haul ass now!"

Serena knew that in one way or another she had crossed the line; she gave Jonas one last kiss and slipped a piece of paper into his hand and ran to catch up with Blair as she stormed out of the bar.

Once outside Blair leaned against the brick wall of the building, gulping down air and trying to calm down before she burst into tears outside a themed pub! It wasn't what Serena said it was the way she had said it, with such distain, lording it over her that Chuck didn't want her that no one ever would. Even a barman from Brooklyn was checking out Serena moments after asking her out. As Serena burst through the doors she stepped forward and tried to hail a cab.

"I thought we had a deal" She turned as she heard Donny's voice behind her

"I said that you could have a date nothing else, I will be ready and willing Friday at 8pm, if you want me bad enough you will find me and if you don't then you don't deserve me."


	2. Chapter 2

**I own nothing, except my car and my collection of shoes and clothes. **

* * *

This is not the best chapter in the world but I think my problem in writing might be trying to make everything too perfect I need to accept that this is still very early days, maybe not every line is going to work or I might make a mistake but hopefully with every story, I will get a little better.

I am really trying very hard to make my triangle even but any constructive criticism would be most welcome.

Thanks and I hope you enjoy.

* * *

"So I can't believe that you actually agreed to share a limo with Blair and Serena!" Nate Archibald joked with his best friend as they waiting outside the Waldorf penthouse to pick up their childhood friends.

"I didn't expect for her to say yes to another ride in my limo" Chuck smirked as he recalled the fun he had had with Blair in the back of that very limousine.

"It's Blair; she never backs down from a challenge" Nate smiled at his best friend, pleased that they could talk about the girl who almost ruined their friendship in the past so openly.

"She also never misses a chance to torture me" Chuck complained swirling the almost full glass of scotch that he was nursing "I never thought that someone could use Friendship as a tool for destruction but Blair is trying"

"I am sure that Blair doesn't plan to torture you its just something that comes naturally to her anyway you are not the only one being tortured. They say you don't know what you have got until it's gone! Man, I dated her almost my whole life, we break up and she turns into a sex kitten. And Serena oh Serena, the way she and Blair have been going on for the past six months has tortured every male in Manhattan; they are constantly plastered over the tabloids falling out of some bar in barely there dresses. They are definitely girls gone wild, I hear that James Martinez has a book running on how long it takes before they are making out with each other in the courtyard." he only half joked.

Chuck eyed his friend from his seat across the limo, just because he and Blair doing the friend thing didn't mean that Nate was allowed to call her a sex kitten or any other sort of kitten he covered his slight annoyance with one of his trademark salacious comments "Now that I would love to see and since Serena is no longer related to me that's something I would pay to be involved with."

"I know your Dad screwed Lily in the divorce and is living in Brooklyn but I don't think Serena is that desperate for cash… yet."

"Must you mention that whore's name? I've just eaten!" he cried out knocking the entire contents of his glass down his throat.

"Lets forget about our parents for just one night its senior year how many more of these parties are we going to go to, the four of us. It's a shock that we can all be friends with everything that has happened I want to enjoy this." Nate pleaded as he refilled Chuck's glass

"Yeah we are all just great friends. The non judging breakfast club!" he mocked downing the second glass as quickly as the first.

"I know things are weird between you and Serena" Nate ventured softly, it was a very sensitive subject

"Her mother left my father for Rufus Humphrey"

"I know but I am pretty sure that she hates what her mother did as much as you do. I mean she has spent the last 3 months staying at Blair's!" Nate reasoned, the Bass – Van Der Woodsen divorce was the biggest news to hit New York in a long time, Lily was desperate to get a quick divorce and Bart was determined to make sure it was as painful and expensive for her as possible. Serena had escaped most of the scandal and the prospect of living across the river by moving into the Waldorf penthouse as soon as Lily had left Bart. "Look all I'm saying is that all our parents are pretty terrible people lets not tear each other apart over their battles. Try to get on tonight Chuck... for me"

"For you Nathaniel... anything." he slurred the shots of alcohol his best friend was dispensing where just topping up the 3 month long binge he had been on since Christmas, he had never imagined that he would have a family so had found himself ill equipped and unprepared when the one he had gotten broke down so dramatically. "As I have always said I care about three things Nathaniel, money, the pleasures money brings me and you!"

Nate laughed to himself as he eyed his best friend, he didn't know if that had ever been true. Despite what his closest friends might believe, he did have the mental acuity to work out that when Chuck had last made that speech he definitely cared about a certain brunette and since then the list had grown to include at least one blonde pseudo-sibling "Do you think we should go up? Blair is going to be pitching a fit."

"I think we should wait down here, you know how I love to get Blair's blood going." Chuck chuckled

"You are a glutton for punishment my man"

"Sometimes the crime is worth the time" Chuck smiled and Nate wondered when the earth had shifted on it's axis, how they had gotten to a stage where his best friend was talking to him like this about the girl he always thought he was going to marry himself.

"I thought you were done with Blair," he stated, his tone shorter than usual, not because he wanted Blair himself but because as much as he loved his boy, Blair wasn't a recent addition to Nate's list of things he cared about. Sometimes she was bumped from the top spot by something new and shiny but she was always there and somehow the thought of Chuck turning her life upside down again made a lump form in his throat.

"I am done with her I just wouldn't mind a trip down memory...limo, what are friends without benefits?" he raised his glass to toast but was left hanging by Nate who suddenly had a very serious expression on his face despite the three bottles of beer had had consumed on the short ride over.

"Like you said to me, if you are done with Blair be done," he said warningly

Chuck obviously didn't hear the warning in his best friends voice as he leaned back and gave his friend the biggest grin Nate had seen since news of Lily's departure had hit gossip girl "I said that because I was having sex with her."

"Man!" was all Nate could manage before the door was ripped open and Blair and Serena tumbled into the car, both sulking, Serena because she had to share a ride with Chuck, and Blair as predicted because the boys hadn't bothered to come up and get them.

* * *

Try as he might Chuck was having a ridiculous amount of trouble tearing his eyes away from Blair backside, ever since she had checked her coat and revealed her scandalously sexy outfit. It was so completely different to anything he had ever seen her in even given the last few months of more and more sexy outfits, and he silently thanked god for Serena moving in and the obvious migration of her clothes into Blair's wardrobe. She was wearing a tiny sequined dress that left almost nothing to the imagination and made her legs go on for miles, on anyone else it might have looked cheap, but on Blair, it looked as ever sexy and sophisticated. She had a way of dictating taste in the UES and girls wearing outfits that Blair would have put together herself just 6 months ago looked stuffy and overdressed. What he couldn't get over was how much she looked like the fun, happy 18 year old she was. Blair had never looked young, despite her doe eyes and dimples; she always looked like she had the weight of the world on her shoulders forcing her to grow up. She was the grown up one and everyone else could be silly because Blair would be there to hold back their hair or pay off who ever needed bribing. He liked this new side of her.

"I'm going to the bar, what's everyone drinking?" Blair asked looking around at the rest of the non judging breakfast club, Serena was checking her phone again, Nate was flashing his million dollar smile in the direction of a couple of girls from Chapin and Chuck was openly checking her out, his eyes slowing ascending up her body until he had locked eyes with her. She could feel the blush rising up her face as the air between them got increasingly thick with sexual tension she licked her lips and saw his eyes dip to watch.

"I'm easy B." Serena replied distractedly too busy looking around the club to notice the intense eye sex that her best friend was in engaging in with her ex-step brother or the way that Nate was sniggering at the double meaning of what she had said.

"Serena who are you looking for?" Blair asked breaking eye contact with Chuck and looking around herself only to see all the usual people she had come to expect at events like this. The host of the party, the daughter of a new money millionaire confectioner, had not had the class to book out the club exclusively but even on a Saturday night the extortionate cover charge and ultra premium liquor meant that the only people around were people they knew. "I don't think your new step brother could deal with either the cover charge or the dress code, it's a surprise your old one did."

"As charming as ever Waldorf, I'll come to the bar with you; I need to assess the choice before making a decision. You know me not easily satisfied with mediocrity" Chuck swarmed as he stood and moved close behind her putting his hand on her waist as he guided her to the bar.

"See mediocre is just the word I would have used to describe Cindy Jacobs" Blair tossed over her shoulder her large smile and twinkling eyes mocking him openly

"Cindy Jacobs?" he asked perplexed for a moment before he remembered, the Blonde with the very discrete belly button boob job, he smiled at the memory and earnt a glare from Blair

"The slut you spent last night with, come on everyone knows Cindy she came back from a summer volunteering at an animal rehabilitation centre in South Africa with breasts like basketballs, as if the world doesn't know that summer volunteering is code for getting work done, either that pregnancy or juvie." Blair rolled her eyes at him

"She asked me if you were coming tonight, before telling me all about your modern day love story, whilst I was trying to eat my sushi. Really Bass, you really should be buying these girls dinner before you show them the "amazing view" from your suite! Are you sure that Dr Sherman hasn't paid you make such vomit worthy stories that I relapse, I know he misses our Wednesday afternoon chats."

"I didn't know you cared" Chuck retorted motioning to the barman for two shots of scotch, he liked Blair best when she was drinking his favourite tipple it seemed to bring out her naughty side. He didn't think that good single malt could be improved upon in terms of taste that was until he tasted it on her lips. The memory of running his tongue around her mouth, tasting scotch, her and sometimes even a little of himself made his trousers feel tight and his pulse feel rapid

"We are friends Chuck, remember." Blair looked up at him her eyes meeting his the picture of innocence as she picked up the tumbler the barman had just filled and rubbed the crystal against her glossy bottom lip before taking a tentative sip. In an instant Chuck remembered how much of a bitch Blair could be and how much of an idiot he was for agreeing to, scratch that suggesting this whole friend thing "When you start sticking it to a girl who is about a week away from the "syph" going to her brain with it makes me worried"

"About that friend thing, Blair...." he begun pushing this own tumbler away suddenly feeling very sober as he attempted to correct his mistakes but he stopped when he realised that Blair wasn't listening, she was looking over his shoulder with her death glare on.

"That little slut" she seethed with an annoyance he hadn't seen since Jenny Humphrey was having her heyday.

"What? Cindy?" he asked wondering what could get under the skin of Blair 2.0, since they had gotten back to school and agreed on the terms of their friendship he hadn't seen her riled up at all. He didn't know if it was because she was genuinely more relaxed or because the idea of a relaxed Blair was so scary that most people just acquiesced to her requests without her having to resort to violence.

"Serena!" she screeched, "she has invited some guy she met in an Irish pub in Brooklyn!"

"Serena, a guy and Brooklyn, I think I might have heard this one before" Chuck dead paned

"That's not the worst of it, he brought his little friend along" pouted Blair as she held her head in her hands

"His friend?" he asked not sure if he wanted to know the answer at all.

"I had a drinking competition with a barman the prize was a date, I lost." She admitted

"Blair Waldorf, what or who has gotten into you, drinking competitions, dates with barmen, sexy little sequined mini dresses and not a headband insight?" he smiled at her with a mixture of lust and admiration and for a second they were both sent back in time, back to before Victrola when Chuck was her wing-man and she his. They would plot and conspire and he would try to corrupt her; both of them naively believing that he would never be able to.

"Blair Waldorf grew up" she sniped shaking away the memory that his smile evoked before grabbing his abandoned glass of scotch and tipping the contents down her throat, she looked up at his shocked expression "sorry were you drinking that?"

"Whoa there, if you don't want to go on a date with him then don't" he reasoned before wiggling his eyebrows and making a playful suggestion "want me to play at being your boyfriend?"

"My boyfriend? How would you sleeping with the next blonde slut that passes help me out of this situation" she joked but neither of them were laughing, this wasn't 2 years ago, and the blonde joke wasn't at Nate's expense anymore, it was at his, that changed everything.

"Look I'll put my arm around you, whisper some sweet nothings," he suggested moving closer to her than he had dared the whole time they had been apart as if to prove his point

"Maybe slip out to the limo for a little limo sex," she questioned raising her eyebrow, challenging him.

"You wish"

"No" she said with a knowing smirk "you wish"

"Do we always have to have this argument?" He looked into her eyes but dropped his gaze as soon as he got a glimpse of the pain behind the smirk

"Bass! He is coming over just do your thing," she whispered hopping onto her bar stool which was quite a feat considering how short her dress was and acting incredibly interested in the exact setting on Chuck's diamond cuff links.

"I found you," Donny whispered into her ear, he had sneaked up behind her which would have shocked her if she hadn't spent the last few seconds practising pretending not to notice him "guess I did want that date bad enough"

"It's not Friday" she threw over her shoulder at Donny trying to ignore the spark of electricity that shot through her body when he spoke into her ear at the same time as ignoring the effect that the obvious jealously on Chuck's face was having on the butterflies which were making a reappearance in her stomach.

"I'm eager what can I say?" he quipped sneakily spinning the bar stool that she was perched on so that they would be face to face

"As much as I would love to be your consolation prize.... Danny" she smiled managing to make him feel ten feet tall and two inches high all at the same time, "I am actually here with my boyfriend"

He eyed her suspiciously and the guy who was standing behind her giving him the evil eye. This guy definitely wasn't defending her in a brotherly way but he was loath to believe that he was her boyfriend, it didn't make sense, Blair wouldn't have agreed to a date if she had a boyfriend and if she did, it certainly wouldn't be this guy with his turquoise suit and ridiculous bowtie "Consolation prize? I have no idea what you are talking about Darlin'"

"she is not your Darling' so why don't you run along" Chuck dismissed the intruder with a wave of his fingers Chuck was getting increasingly annoyed with this guy, flirting with Blair, touching her seat, calling her darling, someone needed to take this guy down a peg or two. He had been moments away from suggesting that Blair come up to the roof with him, he wanted to talk to her, to find out if he was the only one who couldn't get the other out of his head.

"I mean your consolation prize because your buddy got to the "Gorgeous Blonde" before you could." Blair clarified her voice dripping with distain

"Serena is gorgeous but blondes are overrated, I am much more of a fan of Chocolate Curls and fire engine red lips me self." he charmed with a smile on his face, a smile that didn't quite reach his deep blue eyes, which looked annoyed. Blair was used to igniting many feelings in men, in everyone, anger, admiration, lust and loathing but never annoyance. "But if you are that childish that you are still competing with your bessie mate maybe I best stick clear of high school girls."

"Do they pull you aside in Brooklyn and give you some self important right to judge other people?" she slid off her stool and started poking him in the chest to punctuate her words "Who do you think you are?"

"I'm Donny O'Reilly." he replied with a smile and for a second she thought she misheard because the way he was looking at her and the smoothness of his voice was making her think of someone who was definitely not Donny O'Reilly. her head all of a sudden felt dizzy the effects of her two quickly swallowed scotches on a stomach which was empty of anything other than a couple of anti depressants washed down with a glass of champagne started to hit her and she stumbled slightly. Luckily, despite being overwhelmed by just how amazing she looked when she was annoyed Donny was able to quickly grab her waist to stop her from falling and pull her closer to him. She looked up at her saviour, he was gorgeous and she knew there was something special about him. She decided to follow Serena's advice for one in her life and take a chance on a boy from the wrong side of the tracks; it's not as if she could ever develop feelings for someone like Donny O'Reilly! So why not have some fun in the city before she goes to New Haven.

"And I'm Chuck Bass so get your hands off her." the voice barely registered with Donny who was completely in awe of how right it felt to be holding this girl, Blair from Manhattan, it's all he knew, the only information that she offered whilst she was on his turf. Now on her home ground he could see that there was much more to Blair than just some girl from Manhattan. The thought of the princess in his arms both thrilled and scared him, she was the epitome of everything that drew him to New York and everything that made me want to go running back to the green, green grass of home.

He looked down at the beautiful girl in his arms, she had spunk there was something special about her. he decided to take his grandfather's advice for the first time in his life and leave his judgemental side aside and go with his gut, so this guy "Chuck" clearly had the hots for her, and she was bitchy and immature but she was also smart and funny and an O'Reilly never backs down from a bet. He smiled down at Blair who was surprisingly looking up at him with something other than complete hatred and then turned to the boy in blue "Well Chucky boy could you do us a favour and guard Blair's drink because she is coming to dance with me."


	3. Chapter 3

**MWT 3 **

"Rise and Shine sleeping beauty" Nate singsonged as he walked into the suite. The room smelt of cigarettes, alcohol and what Nate was now experienced enough to recognise as sex.

"Nathaniel not quite the sight I expected to wake up to" Chuck stirred on the bed, sitting up and letting the silk sheets pool around his waist "How did you get in here?"

"Your um friends let me in on their way out" he coughed noting the absence of his best friends trademark pyjamas and he quickly turned around to give his best friend some privacy. whilst he waited for Chuck to get dressed his mind drifted back to the last time he had seen those infamous striped jammies, it was two days after Bart's wedding he had come to the suite to sleep guessing the Chuck would be at Blair's only to find his best friend and his ex girlfriend curled up in bed with matching pyjamas on and the menu screen of Charade playing on the plasma screen.

"Oh yes Justine and Jaynie, god bless twins" Chuck smiled as he padded his way from the bed to the shower not bothering to cover himself up.

"I almost forgot about your thing about twins." Nate shouted through the open door of the bathroom as he heard the spray of the shower begin.

"Twice as nice." came Chuck's throaty reply wafting through the steam with the accompanied by the distinctive scent of his $400 shower gel.

"So I've heard" Nate muttered shaking his head and settling himself on the sofa to think about how to include more twins in his own life whilst he waited for Chuck to emerge from the bathroom.

Finally Chuck stepped back into the room, one of the hotels always fluffy and always white towels wrapped around his waist. "Anyway what can I do you for Nathaniel, I have an appointment in about an hour and I don't think that she would appreciate me arriving like this. "

"I just came over to make sure you are OK, I mean you got pretty wasted after Blair went off with that Donny guy." Nate asked concern evident in his voice, Blair had disappeared onto the dance floor with Donny and Chuck had started doing shots. By the time Blair and Donny were on their second dance Chuck was ordering bottles of Patron and by the time they came back to the booth were Nate, Serena and Jonas were waiting after 3 dances Chuck had gone home with no less than three Cheerleaders from Atlanta on a bachelorette weekend in New York.

"Why wouldn't I be OK?" he asked irritated as he roughly flicked through the hangers in his wardrobe looking for a button down shirt "Blair Waldorf finally giving in to type, it was only ever a matter of time."

"I'm just glad you finally listened to my advice" Nate stated as he watched Chuck button up his shirt

"Your advice?" He looked up briefly from his mother of pearl buttons and gave his best friend a confused look.

"About leaving Blair alone, I mean I spoke to Serena this morning and apparently Blair and Donny went out on Friday and Saturday." he explained idly picking at some of night last abandoned room service.

"Yeah I am sure they are love's young dream" Chuck drawled "The barman and the heiress to a billion dollar fortune. I think I saw this once on an episode of CSI: Miami"

"A barman who went to Cambridge and is studying at Columbia Business School," Nate quipped before he could stop himself. He and Serena had fallen into a habit of spending hours on the phone each night and every second that she was telling him about Donny's many qualities was a second she was not listing Jonas'

"Nathaniel remind me to get the concierge to send flowers to your dearly departed Balls!" Chuck joked although his smile didn't seem to reach his eyes. he walked over to his liquor cabinet and poured two drinks "Women gossip, Men drink now if you are not going to join me for some of Scotland's finest please allow me to get ready for my appointment."

"Your appointment hey" Nate smiled his trademark grin and gave his best friend a wink that almost felt like a punch in the stomach as the memories of the last wink came flooding back to him.

Chuck shook away the feeling "Yeah I am meeting a gorgeous brunette, she she looks like that sublime beauty Minka Kelly but younger, hotter and much more adventurous in bed." he joked avoiding his best friend's eyes.

"Sounds amazing" Nate swooned the only thing better than Minka Kelly was Minka Kelly, Megan Fox and Sophia Bush in lots of lots of mud; he definitely needed to get back to Brunettes, and he would... just as soon as he could stop thinking about Serena.

"She is and she isn't one to be kept waiting." Chuck smirked his eyes pointing Nate in the direction of the door.

Nate pulled the door open before turning around and asking his best friend one last time to be sure "Are you sure you are OK about Blair"

"Blair who?" he replied with a look that said one thing _"I'm Chuck Bass"_


	4. Chapter 4

I own nothing!!!

I am trying to make shorter, quicker chapters. But not sure if it's working for me

Hope you are enjoying it, there should be another 7 or so chapters

Also if anyone thinks they could be a quick turn around beta please let me know. I just need someone to look it over and tell me if they get what I'm trying to say....

Enjoy.... PC

* * *

"Thanks for coming Chuck" Blair mewed sipping meekly on her Gin Martini. She was wearing a silk dress in pure white, her dark curls held in place by a gold ribbon, his mind instantly went back to the stories his grandmother would tell him as a boy about the angel looking after his mother in heaven. His grandmother had told him that she too would be with the angels soon and the young Chuck anxious that he wouldn't have anyone to tell him stories once his grandma was visiting his mother in heaven had wanted an angel for himself. Of course, she had told him that he wouldn't have an angel for many many years. Looking at Blair he thought how wrong his grandmother had been, Chuck had met his angel the following September and even though he hadn't know it, even Blair hadn't known it, she had been looking after him his whole life.

"You know that coming for you is my greatest pleasure in life." he quipped like a old Hollywood legend who had been given the script for a porn movie instead of Casablanca as he watched his angel mix him a drink, she always was the Myrna Loy to his William Powell.

"Not your best Bass, rough night?" she asked not truly wanting to know the answer, every night had been a rough night for Chuck since they had gotten back into the city, and since Christmas so had every evening, every study period and most painfully every limo ride.

She recalled the night that Lily had moved out of the family apartment, when she had finally gotten a very drunk and very angry Serena settled into her guest room she had gone over to the half-empty apartment to check on Chuck, as a friend. She had found him sitting in his bedroom, the only room that remained unchanged despite the dissolution of the family, he was drunk more drunk than she had seen him in years, and instead of dismissing her, he allowed her to hold him. He allowed her in, so she ignored the scent of the other women on his clothes the lipstick on his skin afterall friends didn't notice those things and they were friends if nothing else.

"A gentleman never tells"

"Gentlemen are overrated" she admitted as she passed him the cocktail her eyes were saying more than her admission ever could and he knew she wasn't simply responding to that question, she never was, her words were always going back to some past conversation some past life. She was giving him a concession, doors don't slam open but her eyes told him that they sometimes someone could pass you the key to a long locked door when you least expected it.

"Why did you ask me here Blair?" he looked down as he always seemed to in her presence concentrating his attention on the drink she had prepared for him, it was sweet yet dry, fun but classic, plus it was made with his favourite scotch. He licked his lips, in appreciation.

"It's called a _'ceasefire'_" she supplied eyeing his drink a small smile played on her lips as she watched him enjoy the drink "I needed to know something Chuck"

"What, what could you possibly need to know from me? What scotch to buy for your new toy, because I am pretty sure he will prefer a bottle of Poitín!" he joked half-heartedly.

"Chuck don't"

"Don't what Blair?" he asked exasperated

"Don't make this about him," she pleaded reaching out to stroke a piece of fluff from the lapel of his jacket "this isn't about him. It's about us."

"You can't tell me you honestly like him Blair, a barman from Brooklyn!" he spat out incredulously both trying to change the topic and because he couldn't believe that this Donny character was any more than a game. a way of showing the world that Blair Waldorf could indeed do anything, she made the rules and she could break the rules.

"He makes me smile" she whispered quietly, dropping her hands from his jacket and crossing them across her body in an attempt to defend herself or make her words seem more believable. Not realising until then how vulnerable this conversation that she had planned to the last detail would make her feel.

"Not like I do" he trailed a finger down her cheek closing his eyes to relive and relish in the softness of her skin. He would tell himself that he had known Blair long enough, touched her enough times, that the memory of her could not be diminished by time, that his memories of how soft her skin was, how silky her tresses were, accurate. But the reality never failed to blow his mind whether it was her hair flicking across his face as she turned away suddenly or when she would give him the slightest of kisses on his cheek before she left which would have his blood boiling for hours.

"He is smart he understands everything"

"Except you" he countered his voice thick and rough with unspoken emotion

"He likes me" she added her voice almost a whisper; she was doing that thing that he hated again, every conversation, every comment full of thinly veil references to his inferiority.

"I…" he started before turning away sharply. He knew that not telling her was a mistake, but somehow whenever those words lay on his tongue his mouth filled with sand. He should have said it before, too much has happened, too many months of debauchery on both sides, too much pain disguised as friendship, they were ruined, he ruined them. so before he said the words that would destroy them both if he let them he stopped and gave her his trademark smirk. "at least his taste in women is better than his taste in clothing"

"Chuck I need to know if I should keep waiting for you to change your mind." The truth was she really did like him, this barman from Brooklyn for all the reason she said and more but her butterflies were far from dead and she couldn't bear to put them at risk not after they had survived so much, not unless she knew for sure that there was no chance.

"I never asked you to wait Blair"

"I know you didn't but I am and I will. If you tell me that one day you will be able to... to be with me, I will wait ... for as long as it takes." her voice broke on the last few words and the both knew how much it meant, she was willing to give everything up for him, her pride, her future, her chance for a fairytale.

"And if I can't say that?" he challenged not because he wanted to hurt her but because he didn't know what else to do and because he honestly needed to know the answer to the question. If he couldn't be the Prince Charming she needed, if he refused to risk her future by letting her wait for a commitment that might never come, what would be left of them then?

"If you can't say that then I guess we stay what we always were. We are Chuck and Blair, Blair and Chuck, I will be there for you through anything and I know that you will do the same for me. Your darkest thought is my most devilish plan, your worst deed my greatest triumph," she offered, as her heart died a little death. White Knights didn't need ask what would become of the princess if they didn't manage to save her from her ivory tower, they didn't consider whether the princess might actually be happier with the dragon.

"Everything stays the same as it always was friends forever" he mussed more for his own benefit than for hers, saying it aloud he couldn't believe that he hadn't thought of it before, if they never started then they could never be over. I knew that being friends with Blair hurt like hell but the thought of his life without her in it at all was even worse, that would kill him.

"If that's what you want" she choked out her words fumbling out of her mouth as she slammed the door to her heart shut and set about raising her defences.

"It is," he confessed instinctively holding her hand and pressing a kiss onto the smooth skin there.

"To Friends then" she chimed raising the glass in her other hand, he dropped her hand almost as soon as the words left her mouth almost as if hearing them from her made them made the reality of his decision more apparent. She smiled at him quickly wiping away the single tear that dared to escape from her eyes. Even as she glupped down the contents of her drink and watched him walk away she could feel the familiar sensation of bile rising inside her.


	5. Chapter 5

**MWT5 **

Blair leaned up and turned the television off at the wall before turning around to face her boyfriend, they had just watched Breakfast at Tiffany's together for the first time and he had passed the falling asleep test and she intended to reward him, whether he liked it or not. She smiled at him seductively as she crawled back onto his bed.

"So O'Reilly, you never said what your plans were," she purred as she crawled up his body.

"Plans?" Donny spluttered all the blood which was needed in his brain, to work out which of their hundred previous conversations she was referring to, was currently located elsewhere "Well Waldorf my immediate plans involve snogging your socks off" he whispered into her ear before flipping them over and he easily pinned the hands against the pillow above her head and used his free hand to tickle her ribs whilst he kissed her neck.

"Stop it you are so silly" she shrieked through her giggles struggling against his strength to get free from his grip. She ducked her head and managed to catch one of the kisses meant for her neck on her lips enticing a groan from Donny, which signalled the beginning to his end. He deepened the kiss, relaxing as his tongue explored her eager mouth, all thoughts of tickles or socks clear out of his head. She bit his lower lip and he forgot all about holding her hands away and used his previously occupied hand to stroke a path down from her wrists towards her waist. But no sooner had his hands made their journey for pastures new than Blair had taken his distraction for her advantage and flipped them back over and sat as heavily as she could on him trying to pin him to the bed and smiling at the bulge that was pressed against her backside. "I'm serious!" she said breathlessly leaning back as he leaned up to try to recapture her lips "I mean you are working at your Grandfather's bar but soon you will have your masters degree what are you going to do with it? Are you staying here, going back to England, going home to Ireland?"

"What's with the interrogation Blair?" Donny asked irritably ending his pursuit of her lips and flopping back onto the bed beneath her.

His question was like a slap in the face, she looked at him with his floppy dark hair and bright blue eyes and all she saw was Nate, she had fallen back into the needy girlfriend role so quickly she hadn't even realised she was doing it. "I am curious is that a problem?" she asked attempting to climb off him embarrassment radiating from her face.

He grabbed her thighs and held her down afraid that if he didn't she would just put down the shutters he had gotten so used to already in their short time together. "Blair…" he began softly before she cut him off

"It doesn't matter you don't owe me any explanations" she stated coldly as she peeled his fingers away from her legs and extracted herself from his lap. She willed herself to calm down as she walked over to the DVD player and took the disk out before placing it into the case with more concentration than was necessary.

"Blair I like you" he placed his arms around her waist from behind she was barefoot and the height difference meant that her head fitted perfectly into the hollow of his neck "but I have had 5 interviews in New York and no job offers yet well not ones I can take. I can't live with my Granddad and work in his bar me whole life, I don't think the new owner will think kindly of taking on an overpaid pot-boy."

She realised that his frustration was not aimed at her but was because he was stressed out. In her world getting the first job she applied for was a given, just like getting into Yale had been. Everything in her life had been a given, her route planned out from birth, she had even made an allowance for falling for a guy like Donny. She figured it would be in college, she and Nate would be on a break and she would have a passionate affair with a middle class political science major, she imagined herself going to rallies in Washington and drinking cheap beer in student bars, growing her hair out and wearing corduroy. But even in her plans their relationship was doomed eventually the differences in their circumstances would come between them, it would be a fight about financial aid that would drive her back into the arms of a Nate who hadn't realised how much he loved her until he had lost her. She was saddened at the thought that even in her daydreams other people were merely catalysts for the advancement of her own agenda. She and Donny would never fight over financial aid, he wasn't a lefty socialist, he was a walking advert for the American dream, successful, driven, ambitious. Gossip girl may have dubbed him Brooklyn Boy - Part Duex but he didn't share any of Dan's distain for the Upper East Side, nor did he try to pretend he was part of it like Jenny. In short, he was perfect, even more so because rich or poor he was more like her than even her closest friends were, everything he got he had to work for and Blair knew all about that. "So Cormack is really going to sell the place?" she asked softly turning around in his arms to look up at him.

"It looks like it I come here to get to know me Grandpa and as soon as I land he starts pinning for the green green grass of home."

"That song was written about a guy in prison you know." She smirked up at him.

"Alright smartass" he laughed kissing the end of her nose and leading her back towards the bed.

"How is it that Serena and I walk into a bar in Brooklyn and she meets a Greek shipping heir and I meet you? Everyone knows that she likes Brooklyn boys." She mused dropping his hand and walking over to the window to look out on the Brooklyn street that Donny lived on with his grandfather, it wasn't the worst area she guessed. Less pretentious than the yuppie paradise that the Humphreys lived in and compared to the rat-infested hole that Vanessa lived it was like the Ritz. Sometimes when Donny was busy working or studying, she would come to the window and look out watching children out with their parents not their nanny's, seeing a guy walk a girl home after a date instead of getting the driver to drop her off. From her place at the window, she could pretend to be anyone she wanted, to have any life she wanted. Even Gossip girl did not go this far out, it was calming not having to live up to anyone's expectations, she loved it and sometimes she even thought she might love Donny for allowing her to have a glimpse into this life.

"I am going to try very hard not to be offended by that comment." Donny laughed throwing a pillow at her and missing completely "Anyway, I have an interview tomorrow; and if I get it, I might even be able to move to your side of the bridge."

Her stomach clenched at the idea of Donny moving to Manhattan unsure if it was fear or excitement she changed the topic. "What and miss out on Cormack O'Reilly's Full Irish breakfasts, You can leave if you want but I'm staying, hey you can have Eleanor, we could do a house swap! We both know how much she adores you."

"She does seem completely powerless against my charms" he joked smiling ear to ear and jumping up to grab her by the waist and attempt to pull her to the bed again.

"You know when I bought you home, I thought the Irish, Catholic, Barman son of a single mother from Brooklyn could possibly be someone who my mother likes less than me but no she loves you." Blair half-joked finally giving in and joining Donny on the bed. Eleanor seemed completely enamoured with Donny from the moment she met him. It helped that his favourite professor also happened to be one of her boyfriend Cyrus' best friends, and that his summer of working as a tour guide at Blarney Castle had given him a fair few kisses of the stone and a definite gift of the gab.

"Well apart from my obvious charms, I am a Cambridge Graduate and soon to have my Masters from Columbia!" he reasoned slinging one arm around Blair as he reached towards his textbook with the other; trying to ignore the feeling in the pit of his stomach that their relationship was just a way of Blair rebelling, just like her being in his grandfather's bar had been. This is how they spent Sundays, watching movies and studying in bed, hers or his it did not matter as long as they were together. Despite their steamy interludes, it was the most PG friendly relationship either had been in for a very long time, and Donny was more than happy to keep it that way, at least until he was sure about her feelings. At first it had been an exercise in restraint, Blair had wanted to know that he really liked her before she opened herself up to him, but over the weeks it had changed and as much as she felt ready she realised that the decision about when to take the next step was no longer hers. She didn't understand it especially considering the clear physical effect she had on him, but she wouldn't push it, she wouldn't be the girl trying to seduce her boyfriend again even if sometimes she felt like she was dating Serena but with more kisses.

"My Mom never bothered much about academics or experience it's all about aesthetics with Eleanor and you are a hottie" she joked leaning her head back against his chest and relaxing into his embrace.

"Aye, that's why the auld lad loves you; you make him wish he was 40 years younger!"

They sat in silence for almost an hour, Donny reading about Derivatives and Blair reading her AP English text. "Do you ever think about finding your Dad, I mean he lives in New York you could be passing him every day without knowing." Blair wondered aloud breaking the comfortable silence, which was beginning to bore her.

Donny sighed and put his textbook down "I never really missed not having one, I don't know all I know about my father is that he was my Ma's boss and they had a bit of a thing going. My ma loved the bones of him but one day he ended things said that he had fallen for some socialite, by the time me Ma realised she was pregnant he was engaged."

"Where did your mom work in that year?" Blair asked craning her neck to look up at him her automatic response to mystery was to investigate.

"I don't know Columbo; ask Cormack he knows all about that stuff" he half joked before taking a more serious tone "I'm not really interested about a man who dumped me Mother for someone with more money. He probably has a family now he doesn't want me turning up on his doorstep I say let sleeping dogs lie"

She turned towards him kneeling on the bed so she could tell him the news that had been going around her head for the best part of a week. "Speaking of old dogs, Roman and my dad have invited you to the vineyard this summer, I will be there for a few weeks before Serena and I go around Europe. We are flying out in the Bass jet since using it whenever she likes is the only concession Bart granted Lily in the divorce and Jonas is flying back to New York a week after we land so you could fly back with him"

"Wow you have it all planned out" Donny breathed "meeting your pa that's pretty intense"

"Too intense?" Blair questioned, fearing that she had managed to make the same mistake twice, what was it about her wanting to go to Europe with guys. "I just thought it would be a nice to spend some time together before I go to New Haven. But if it's too intense for you then don't worry about it, I guess you want to stay in the city and have fun!" she shouted packing her book into her nearby bag and jumping out of bed readying herself to leave.

"If I get this job I will be working 80 hour weeks I won't have time to have fun. Blair I like you a huge amount and I want us to work!" he pleaded following her up and grabbing her hand to kiss her knuckles "I can't wait to spend my weekends in New Haven."

"Walks around campus, cosy dinners in little cafes." She purred lightly kissing her way from his ear down to his neck as her fingers made light work of the buttons on his shirt. This is how it always was with them, an argument would turn into passion in an instant, whether they were at home, or in a club even once when the argument was because she had insisted that she could ride the subway like any other New Yorker and then complained about the seats not being comfortable. That particular argument had resulted in Donny being attacked with an umbrella by a little old lady who said that they would both end up in hell for their behaviour.

He dropped his hands from her waist to cup her buttocks lifting her slightly so that she could wrap her legs around his waist lifting her even higher so that he could nuzzle her breasts through her thin blouse "Or we could just make sure your parents get their money's worth out of your dorm room, you did get a single didn't you." he murmured against her breasts

"You are heinous Bass." She joked laughing against his dark head not realising her mistake until she found herself unceremoniously lowered to the floor.

"O'Reilly, Blair my name is Donald O'Reilly" he spat out turning on his heels away from her

"Donald, I'm sorry I'm so so sorry, it's just I guess sometimes you remind me of him" she explained to his back. The instant she said it she realised that she had made another mistake; she didn't want Donny to think that she was thinking of Chuck whenever they were together, no matter how much sometimes the two dark haired boys blended in her mind. "No it's not that, it's just things you say, sometimes when you look at me, he has been one of my best friends for 14 years Donny come on don't make this into something it isn't. It's not like I called you Nate!"

"Oh yeah Nate your other best friend slash guy who you've slept with that you hang out with all the time. But then again I would never remind you of the gorgeous amazing Nathaniel Archibald." He roared turning to face her, his arm flailing in frustration.

"I thought I was the insecure high school kid!" she countered shoving her feet into her nearby Louboutins which with their trademark scarlet 5 inch heels almost levelled the height difference. She stared into his eyes, they were the brightest blue, like the sea or a swimming blue but when she looked into them all she saw was fire. Fire she had never seen in eyes so blue, it warmed her in a way that Nate's cold aqua eyes never did and melted her resolve somewhat. "Donny I am with you. Nate and Chuck are my best friends but all they ever did was hurt me, you make me happy."

"It's hard Blair, You are like a princess, a Waldorf with these two amazing princes around you all the time, I am just a pauper I don't have anything to give you but my heart." He admitted leaning his head on her shoulder

"Well that is something that no one has ever given me," she whispered softly as she stroked his black-brown silky hair and desperately tried not to think of Chuck "I choose you Donny"


End file.
